Piperidine → 2,3-Diphenyl-4-(piperidin-1-ylmethyl)pyridine

HRID 80306ノート

反応式

HRID 80306 の反応式
S(Cl)(Cl)=O.[C:5]1([C:11]2[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:13][CH:14]=[CH:15][C:16]=2[CH2:17]O)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[NH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1.C(=O)([O-])O.[Na+]>>[C:5]1([C:11]2[C:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:13][CH:14]=[CH:15][C:16]=2[CH2:17][N:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

参加物

5

反応物 4

HCID 8082PiperidineHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 67428383[Diphenyl(4-pyridyl)]methanol

生成物 1

HCID 674274232,3-Diphenyl-4-(piperidin-1-ylmethyl)pyridine収率 71%

実験手順

Thionyl chloride (1 mL) (Wako Pure Chemical Industries, Ltd.) was added to Compound 9 described above (0.30 g, 1.15 mmol), and the mixture was refluxed for 30 minutes. Then, the solvent was distilled off under reduced pressure. The residue was dissolved in acetonitrile (20 mL), and piperidine (0.75 g, 8.80 mmol) (Wako Pure Chemical Industries, Ltd.) was added thereto, followed by reflux for 3 hours. The mixture was returned to room temperature, and then a saturated aqueous solution of sodium hydrogen carbonate (Wako Pure Chemical Industries, Ltd.) was added thereto, followed by extraction with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.) as an eluent), to thereby obtain the title compound (0.27 g, 71% yield).

後処理

  1. temperaturethe mixture was refluxed for 30 minutes
  2. distillationThen, the solvent was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in acetonitrile (20 mL)
  4. temperatureby reflux for 3 hours
  5. customwas returned to room temperature
  6. extractionfollowed by extraction with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  8. distillationthe solvent was distilled off under reduced pressure

出典と根拠

ORDレコード
ord-4942ef47a8bb4a0f835063670b77b5c0
出典データセット
uspto-grants-2014_09
特許番号
US08846012B2

反応ノート

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